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17 Ways to Wear Thigh-High Boots This Winter

Whether they’re leather or suede, flat-soled or with block heels, thigh high boots aren’t only surprisingly wearable, but they’re well on their way to becoming cold-weather wardrobe staples. Pull them on over skinny jeans or leggings, style them with a midi skirt that falls below the top of the boot, or allow a sliver of skin (or tights, come winter frost!) to peek out between your boot and a short hemline. Just in time for winter, find our 17 favorite ways to wear thigh high boots, below.

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PHOTO: Edward Berthelot

To make your Canadian tuxedo winter-ready, swap the open-toe heels for knee high-boots.

Shop the look: Stuart Weitzman Emiline Boots, $898 $449, Shopbop

Street Style - Copenhagen - December 12, 2018

PHOTO: Christian Vierig

Snakeskin adds texture to any outfit—statement boots like these just make it that much easier.

Shop the look: Mango Snake-Effect Boots, $129.99 $79.99, Mango

Celebrity Sightings In Los Angeles - December 13, 2016

PHOTO: BG005/Bauer-Griffin

What’s more fall than an oversized turtleneck, skinny jeans, and over-the-knee suede boots? All that’s missing is a peppermint-flavored beverage.

Shop the look: Barneys New York Faux-Suede Over-the-Knee Boots, $799 $136, Barney’s Warehouse

Street Style : Paris Fashion Week Womenswear Spring/Summer 2018 : Day Six

PHOTO: Claudio Lavenia

Even when layered under longer silhouettes, your knee-high boots can still pack a punch. This neon green pair stands out under all those slick layers.

Shop the look: Forever21 Yoki Ribbed Over-the-Knee Sock Boots, $48 $38.40, Forever21

Street Style : Day Nine - Paris Fashion Week Spring/Summer 2017

PHOTO: Vanni Bassetti

Wear that plain long-sleeved midi dress to one of your holiday parties with some silver boots. Unexpectedly festive.

Shop the look: Marc Fisher Pagie Over the Knee Boot, $149.99 $89.98, DSW

Celebrity Sightings in New York City - April 20, 2017

PHOTO: Ray Tamarra

Knee-high and over-the-knee boots are a great footwear style to help transition your mini dresses and skirts into the colder months. Match the hemline with the top opening of the shoe, and top off with an oversized coat.

Shop the look: & Other Stories Knee High Suede Boots, $279, & Other Stories

Street Style By Timur Emek - LFW February 2017

PHOTO: Timur Emek

Breathe new life into that pencil skirt with heeled knee-high boots this winter. In lieu of a blazer, top the outfit off with a sleek leather jacket.

Shop the look: Hai Knee High Boot, $199.95 $79.98, Nordstrom

Street Style : Paris Fashion Week Womenswear Spring/Summer 2018 : Day Eight

PHOTO: Edward Berthelot

Even your shorts can be winter-ready, thanks to some over-the-knee boots.

Shop the look: Jeffrey Campbell Obey Tall Boots, $175 $52.50, Shopbop

Street Style - Paris Fashion Week - Haute Couture Fall/Winter 2017-2018 : Day Two

PHOTO: Christian Vierig

A short hemline puts the spotlight on the shoes. Don’t shy away from it.

Shop the look: Iro Ava Boots, $1,090 $763, Shopbop

Street Style : Paris Fashion Week Womenswear Spring/Summer 2018 : Day Three

PHOTO: Timur Emek

Here’s a winter outfit formula that never, ever fails: a striped sweater plus light-wash skinny jeans plus black suede boots.

Shop the look: Rachel Comey Zim Boots, $550 $385, Shopbop

Street Style - New York Fashion Week February 2017 - Day 6

PHOTO: Christian Vierig

When in doubt, go for a black-on-black look: Layer a knit dress over a sheer turtleneck and tights, and top off the look with some combat-style knee-high boots.

Shop the look: Coach Westerly Tall Boot, $185, Coach

Celebrity Sightings in New York City - October 5, 2017

PHOTO: James Devaney

To make your boots the center of attention, stick to a muted color palette for the rest of your ensemble.

Shop the look: Sam Edelman Hai Knee High Boot, $199.95 $79.98 Nordstrom

Street Style : Day Eight - Paris Fashion Week Womenswear Fall/Winter 2017/2018

PHOTO: Christian Vierig

Alternatively, a pair of black over-the-knee boots can play down the sweetness of a really bright garment—like, say, a hot-pink playsuit.

Shop the look: Coach Giselle Over The Knee Boot, $495 $247.50, Coach

Street Style : Paris Fashion Week Womenswear Spring/Summer 2018 : Day Four

PHOTO: Timur Emek

You don’t have to overthink the oversized sweatshirt-as-dress when you pair it with knee-high boots.

Shop the look: Dorateymur Town & Country Tall Boots, $680 $272, Shopbop

New York Fashion Week - Street Style - Day 3

PHOTO: Daniel Zuchnik

A different take on wintry monochromatic dressing—try head-to-toe burgundy this season.

Shop the look: Mango Leather High-Leg Boots, $249.99 $124.99, Mango

Celebrity Sightings in New York City - October 12, 2017

PHOTO: James Devaney

Celebrities can’t get enough of the slouchy boot silhouette. The key is to keep the rest of your ensemble sleek and streamlined, so that the shapes balance each other.

Shop the look: Coach Graham Slouchy Boot, $450 $225, Coach

New York Fashion Week - Street Style - Day 4

PHOTO: Matthew Sperzel

A high-slit skirt is no problem in the winter with an extra-extra-high boot.

Shop the look: ASOS Design Kera Pointed Thigh High Boots, $76 $60.50, ASOS

Related Stories:

20 Essential Over-the-Knee Boots to Buy This Season

35 Perfect Street-Style Outfits for Any and All Party Dressing Scenarios

The One Item I Buy in Bulk from ASOS

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